HCID 21875993, compound → HCID 21876484, compound

HRID 967845Notes

Reaction equation

HRID 967845 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][OH:15])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 21875993HCID 21875993, compound

Product 1

HCID 21876484HCID 21876484, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2-[4-(2-nitroanilino)phenyl]ethanol (2.0 g, 7.6 mmol) in methanol (15 mL) was added 10% Pd—C (160 mg). The mixture was stirred at room temperature for 6 h under hydrogen atmosphere. The palladium catalyst was removed by filtration and washed with ethanol (100 mL). The filtrate was concentrated under reduced pressure to afford 1.6 g (92%) of the title compound as pale yellow solids: 1H-NMR (CDCl3)δ2.79 (2H, t, J=6.6 Hz), 3.75 (2H, br), 3.80 (2H, t, J=6.6 Hz), 5.14 (1H, s), 6.82-6.66 (4H, m), 7.15-6.96 (4H, m).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. washwashed with ethanol (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bba7a9e0abb44c72a43b1f70b517ca34
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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